Our 2025 CEOs to Watch are forward-thinking leaders transforming family businesses across generations and industries. Some are building values-driven enterprises from the ground up, others are modernizing multigenerational companies. Some are family members, others are not. But they’re all united by a shared commitment to creating inclusive, purpose-driven cultures that blend innovation and tradition.
They also have another trait in common: the ability to balance long-term vision with day-to-day execution, ensuring their companies remain competitive while staying grounded in the family’s values.
Robert Wilson
Employco | Founder & CEO | First Generation
Since co-founding Employco USA in 1996 alongside his brother and father, Robert Wilson has grown the company from a small family start-up into a highly successful HR outsourcing firm with more than $600 million in sales.
“What really sets Rob apart is his ability to combine big-picture vision with a people-first approach,” says his son, Griffen Wilson, who serves as Employco’s vice president. “He’s always kept Employco ahead of the curve by embracing new technologies and creating innovative solutions that make life easier for clients and help them navigate the ever-changing regulatory landscape.”
Wilson’s leadership has been tested — and proven — through several major challenges. Each time, he found ways to pivot, enter new markets and build strategies that kept both clients and employees secure. For example, during the COVID-19 pandemic, he personally led more than 45 webinars to guide clients through the uncertainty and help them secure PPP loans, demonstrating just how deeply he cares about the people he serves.
Wilson is known for his open-door policy and his genuine belief that employees are the company’s greatest asset. Griffen credits his father with building a culture where everyone feels empowered, motivated and valued. “Rob’s journey — from starting out with just $5,000 in sales to leading an industry powerhouse — is a testament to his grit, integrity and unwavering commitment to his family and his team.”
Beyond Employco, Wilson is also committed to his community, serving on several Young Professionals Organization boards, as well as the Chicago Police Foundation Board and the ESCA Board.
“I was drawn to entrepreneurship at an early age because of my father, who started his company when I was in eighth grade,” Wilson recalls. “I started my first business when I was in college, managing rock bands and opening a record company from my fraternity house. In 1996 we saw an opportunity to work together and build a business that provides HR solutions to small business across the country that were unanswered. It was a great opportunity to work together with a shared vision to create a new business filling a void to small businesses. I’ll never forget my dad saying, ‘How hard can it be? Let’s do this!”